ES2104376T3 - Agente de alquilacion y procedimiento para la reaccion por adicion en 1,4 de un grupo alquilo con un compuesto con ceto insaturado en alfa,beta. - Google Patents
Agente de alquilacion y procedimiento para la reaccion por adicion en 1,4 de un grupo alquilo con un compuesto con ceto insaturado en alfa,beta.Info
- Publication number
- ES2104376T3 ES2104376T3 ES94913090T ES94913090T ES2104376T3 ES 2104376 T3 ES2104376 T3 ES 2104376T3 ES 94913090 T ES94913090 T ES 94913090T ES 94913090 T ES94913090 T ES 94913090T ES 2104376 T3 ES2104376 T3 ES 2104376T3
- Authority
- ES
- Spain
- Prior art keywords
- beta
- pct
- alpha
- addition
- unsaturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- KJDGFQJCHFJTRH-YONAWACDSA-N 16-Ketoestradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@H](C(=O)C4)O)[C@@H]4[C@@H]3CCC2=C1 KJDGFQJCHFJTRH-YONAWACDSA-N 0.000 title 1
- 229930194542 Keto Natural products 0.000 title 1
- 239000002168 alkylating agent Substances 0.000 abstract 3
- 229940100198 alkylating agent Drugs 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 abstract 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical group [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/02—Addition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0025—Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
LA PRESENTE INVENCION DESCRIBE UN MEDIO DE ALQUILIZACION, CONTENIENDO UN REACTIVO DE ALUMINIO ALK{SUB,3}-{SUB,M}ALL{SUB,M}, DONDE ALK SIGNIFICA UN GRUPO METILO, ETILO, N - O I - PROPILO, N -, I - O BUTILO TERCIARIO, GRUPO PENTILO, HEXILO, HEPTILO O GRUPO OCTILO, DE FORMA QUE TODOS ELLOS PUEDEN SER TAMBIEN RAMIFICADOS, L ES UN GRUPO ETOXI, UN ATOMO DE CLORO O DE BROMO Y M ES IGUAL A 1 O 2, COMO FUENTE ALQUILO O TAMBIEN DIMETILO DE ZINC COMO FUENTE METILO, QUE ADICIONALMENTE PUEDEN SER CANTIDADES CATALITICAS DE UNO O MULTIPLES COMPUESTOS DE COBRE I Y/O COBRE II Y UNO O (MULTIPLES) REACTIVOS SILILO DE LA FORMULA GENERAL (III): R{SUB,1}R{SUB,2}R{SUB,3}SIZ, DONDE R{SUB,1}, R{SUB,2} Y R{SUB,3} PUEDEN SER IGUALES O DIFERENTES Y REPRESENTAN UN RESTO ALQUILO DE CADENA RECTA O RAMIFICADA CON UNO EN O EN CASO DE CADENA RAMIFICADA 3 HASTA 10 ATOMOS DE CARBONO, UN GRUPO ALCOXI DE CADENA RECTA O RAMIFICADA CON 1 HASTA 3 ATOMOS DE CLORO O UN RESTO ALQUILO CON UNO O EN CASO DE CADENA RAMIFICADA 3 HASTA 6 ATOMOS DE CARBONO CON RESTO ALQUILO SUSTITUIDO, ASI COMO Z ES UN ATOMO DE CLORO, BROMO O YODO, RESTO CIANO, UN RESTO PERFLUOR ALQUILO SULFONILO [(C{SUB,N}F{SUB,2N+1SO{SUB,2}O-) CON N = 1, 2, 3 O 4], EL RESTO MESILATO CH{SUB,3}SO{SUB,2}O -, RESTO TOSILO P CH{SUB,3} - C{SUB,6}H{SUB,4} - SO{SUB,2}O - O UN OTRO GRUPO DE PARTIDA. ASI COMO UN PROCEDIMIENTO PARA 1,4 - ADICION DE UN GRUPO ALQUILO EN UN {AL}, {BE} - CETO NO SATURADO O EN UN {AL}, {BE} CETO SATURADO DOBLE O EN UN {AL}, {BE} - ALDEHIDO NO SATURADO BAJO UTILIZACION DEL MEDIO DE ACUERDO CON LA INVENCION. EL MEDIO DE ALQUILIZACION SUMINISTRA COMPUESTOS ACTIVOS BIOLOGICOS EN RENDIMIENTO SOBRESALIENTE Y EN BASE A UN CKW (CLORO HIDROCARBUROS) MEDIOS DE REACCION LIBRES QUE SE CARACTERIZAN DE FORMA QUE SE OBTIENE UN NUEVO PROCEDIMIENTO DE MEDIO DE ALQUILIZACION A TRAVES DE SU TOLERABILIDAD AL MEDIO AMBIENTE.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4311028A DE4311028A1 (de) | 1993-03-30 | 1993-03-30 | Methylierungs- bzw. Ethylierungsmittel und Verfahren zur 1,4-Addition einer Methyl- bzw. Ethylgruppe an eine alpha,beta-ungesättigte Keto-Verbindung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2104376T3 true ES2104376T3 (es) | 1997-10-01 |
Family
ID=6484689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES94913090T Expired - Lifetime ES2104376T3 (es) | 1993-03-30 | 1994-03-30 | Agente de alquilacion y procedimiento para la reaccion por adicion en 1,4 de un grupo alquilo con un compuesto con ceto insaturado en alfa,beta. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5908945A (es) |
| EP (1) | EP0691974B1 (es) |
| JP (1) | JP3492368B2 (es) |
| AT (1) | ATE152726T1 (es) |
| CA (1) | CA2172816C (es) |
| DE (2) | DE4311028A1 (es) |
| DK (1) | DK0691974T3 (es) |
| ES (1) | ES2104376T3 (es) |
| GR (1) | GR3023957T3 (es) |
| WO (1) | WO1994022878A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19743165A1 (de) * | 1997-09-30 | 1999-04-01 | Studiengesellschaft Kohle Mbh | Selektive Alkylierung von Aromaten mit oberflächenmodifizierten mikroporösen Mischoxiden |
| CN114395007B (zh) * | 2021-12-28 | 2023-03-24 | 江西君业生物制药有限公司 | 一种美睾酮的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2927086A (en) * | 1958-03-27 | 1960-03-01 | Pan American Petroleum Corp | Alkylation process and catalyst |
| DE1122944B (de) * | 1960-04-06 | 1962-02-01 | Schering Ag | Verfahren zur Herstellung von 1ª‡-Methyl-3-ketosteroiden |
| US3065253A (en) * | 1960-12-27 | 1962-11-20 | Gen Electric | Process for the alkylation of halogenosilanes |
| DE4132755A1 (de) * | 1991-09-27 | 1993-04-01 | Schering Ag | Methylierungs- bzw. ethylierungsmittel und verfahren zur 1,4-addition einer methyl- bzw. ethylgruppe an eine (alpha),(beta)-ungesaettigte keto-verbindung |
-
1993
- 1993-03-30 DE DE4311028A patent/DE4311028A1/de not_active Withdrawn
-
1994
- 1994-03-30 EP EP94913090A patent/EP0691974B1/de not_active Expired - Lifetime
- 1994-03-30 DK DK94913090.0T patent/DK0691974T3/da active
- 1994-03-30 AT AT94913090T patent/ATE152726T1/de not_active IP Right Cessation
- 1994-03-30 DE DE59402671T patent/DE59402671D1/de not_active Expired - Fee Related
- 1994-03-30 ES ES94913090T patent/ES2104376T3/es not_active Expired - Lifetime
- 1994-03-30 CA CA002172816A patent/CA2172816C/en not_active Expired - Fee Related
- 1994-03-30 WO PCT/EP1994/001001 patent/WO1994022878A1/de not_active Ceased
- 1994-03-30 US US08/530,155 patent/US5908945A/en not_active Expired - Fee Related
- 1994-03-30 JP JP52167294A patent/JP3492368B2/ja not_active Expired - Fee Related
-
1997
- 1997-06-30 GR GR970401607T patent/GR3023957T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994022878A1 (de) | 1994-10-13 |
| EP0691974A1 (de) | 1996-01-17 |
| DK0691974T3 (da) | 1997-12-08 |
| DE59402671D1 (de) | 1997-06-12 |
| EP0691974B1 (de) | 1997-05-07 |
| CA2172816C (en) | 2003-05-06 |
| CA2172816A1 (en) | 1994-10-13 |
| JPH09503741A (ja) | 1997-04-15 |
| DE4311028A1 (de) | 1994-10-06 |
| JP3492368B2 (ja) | 2004-02-03 |
| US5908945A (en) | 1999-06-01 |
| GR3023957T3 (en) | 1997-09-30 |
| ATE152726T1 (de) | 1997-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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